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https://elib.bsu.by/handle/123456789/258083
Title: | From 2- to 3-Substituted Ferrocene Carboxamides or How to Apply Halogen "dance" to the Ferrocene Series |
Authors: | Tazi, M. Erb, W. Halauko, Y.S. Ivashkevich, O.A. Matulis, V.E. Roisnel, T. Dorcet, V. Mongin, F. F. |
Keywords: | ЭБ БГУ::ЕСТЕСТВЕННЫЕ И ТОЧНЫЕ НАУКИ::Химия |
Issue Date: | 2017 |
Publisher: | American Chemical Society |
Citation: | Organometallics 2017;36(24):4770-4778. |
Abstract: | Two methods were compared to convert ferrocene into N,N-diisopropylferrocenecarboxamide, N,N-diethylferrocenecarboxamide, N,N-dimethylferrocenecarboxamide, and (4-morpholinocarbonyl)ferrocene, namely, deprotometalation followed by trapping using dialkylcarbamoyl chlorides and amide formation from the intermediate carboxylic acid. The four ferrocenecarboxamides were functionalized at C2 in the case of the less hindered and more sensitive amides, recourse to a mixed lithium-zinc 2,2,6,6-tetramethylpiperidino-based base allowed us to achieve the reactions. Halogen migration using lithium amides was next optimized. Whereas it appeared impossible to isolate the less hindered 3-iodoferrocenecarboxamides, 3-iodo-N,N-diisopropylferrocenecarboxamide proved stable and was converted to new 1,3-disubstituted ferrocenes by Suzuki coupling or amide reduction. DFT calculations were used to rationalize the results obtained. |
URI: | https://elib.bsu.by/handle/123456789/258083 |
DOI: | 10.1021/acs.organomet.7b00659 |
Scopus: | 85041216154 |
Sponsorship: | Minister̀ e de lʼEnseignement supeŕ ieur, de la Recherche et de lʼInnovation (grant to M.T.) and the Université de Rennes 1. We also thank the Centre National de la Recherche Scientifique, the Institut Universitaire de France and Rennes Met́ ropole. We acknowledge FEDER founds (D8 VENTURE Bruker AXS diffractometer) and Thermofisher (generous gift of H-TMP). |
Appears in Collections: | Статьи сотрудников НИИ ФХП |
Files in This Item:
File | Description | Size | Format | |
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From 2- to 3-Substituted Ferrocene Carboxamides_accepted.pdf | 1,43 MB | Adobe PDF | View/Open |
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